Triphenylphosphine → HCID 53959493, compound

HRID 363067Notes

Reaction equation

HRID 363067 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20](O)[CH:21]=[CH:22][C:23]=1OCC.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:31]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:30][CH2:31][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:28])[F:29])[CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 573614134-Ethoxy-3-(trifluoromethyl)phenol

Product 1

HCID 53959493HCID 53959493, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.20 g of 3-(trifluoromethyl)phenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.39 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-(trifluoromethyl) phenyl)ethoxy)benzene (81% yield), nD26.0 1.5497.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain a residue

Sources & evidence

ORD record
ord-4e10b8ffaf6242bf886f44c9aaef2c53
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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